The area known today as Montreal had been inhabited by the Algonquins, Huron, and Iroquois for some 2,000 years, while the oldest known artifact found in Montréal proper is about 2,000 years old.[1]

In the earliest oral history, the Algonquins were from the Atlantic coast. Together with other Anicinàpek, they arrived at the "First Stopping Place" (Montréal). There, the Nation found a "turtle-shaped island" marked by miigis (cowrie) shells.

The Iroquois or Haudenosaunee were centred from at least 1000 CE in northern New York, but their influence extended into what is now southern Ontario and the Montréal area of modern Quebec.[2]

1535 – Jacques Cartier renames the Saint Lawrence River in honour of the Deacon Lawrence on August 10 (Feast day of the Roman martyr). Prior to this, the Saint Lawrence River had been known by other names, including the Hochelaga River and the Canada River. Cartier penetrates far into the interior for the first time, via the river.

1535 – September 19, Cartier starts his journey from Quebec City to Montréal, while in search of a passage to Asia.

1535 – Cartier visits Hochelaga on October 2, claiming the St. Lawrence Valley for France.[6] He becomes the first European to reach the area now known as Montréal when he enters the village of Hochelega. Cartier estimates the population to be "over a thousand".

1535 – October 3, Cartier climbs up the mountain on the Île de Montréal and names it Mont Royal. He wrote: "Nous nommasmes icelle montaigne le mont Royal." (We named the said mountain Mont Royal.) The name Montréal is generally thought to be derived from "Mont Royal", the name given to the mountain by Cartier in 1535.

1645 – The hospital is initially located within the fort. Maisonneuve grants the first concession outside the fortifications to Jeanne Mance so that she could build Hôtel-Dieu de Montréal; work begins on it on October 8, 1645.

1653 – The Grande Recrue: Jeanne Mance takes money that was intended for the hospital and uses it to recruit a hundred people; the contingent arrives at Ville-Marie on November 16. Of the 95 who embark in Saint-Nazaire, 24 are massacred by Iroquois; 4 drown; one is burnt when his house catches fire.[10]

1666 – According to census of New France, Ville-Marie now has 582 inhabitants. 24 of the 111 families living in Montréal had already been formed in France. A few houses, flanked by a windmill and fort, and connected by a footpath where now runs Rue Saint-Paul, represent the beginnings of Ville-Marie.

1667 – Almost from its foundation, pelts were bartered in Montreal, but it was after 1667 that the town becomes a centre for trade. An annual market for pelts takes place in June on the common of Pointe-à-Callière.

1670-80 – At first trading is done in people's home, but traders soon set up stalls between Rue Saint-Paul and the Little St. Pierre River, west of the marketplace. Natives – some 900 of them in 1672 – camp on the point.

1680-85 – More and more voyageurs, coureurs des bois and missionaries were exploring the regions upriver from Montreal. As the new territory opens up, part of the fur trade shifts toward the Great Lakes. Fewer and fewer natives came to Montreal, and the annual fur fair became less popular from 1680 to 1685.

1687 – An epidemic of typhus kills approximately 150 people in the autumn.

1689 – On June 13, construction was begun by the Montreal Sulpicians on a 2 km canal to support their monopoly on flour-milling. François Dollier de Casson asserts that such a canal (Lachine Canal) would supply water to Montreal's mills while simultaneously facilitating westbound navigation.

1698 – A chapel dedicated to St. Anne is founded at the south end of Murray street. Le Quartier Ste-Anne becomes infamous as a den of licentiousness, and the clergy restricts the sale of liquor around the chapel.

1698 – Bishop Saint-Vallier, returning from France, accompanies two English gentlemen, one of them a Protestant minister, on a visit to Jeanne Le Ber.

1700 – At the turn of the 18th century Montreal's population is about 1,500 souls, which gradually grows to about 7,500 in the year 1760, at the time of the British conquest.

1711 – The court orders the construction of a stone wall around the city.

1713 – Jurisdiction of the Government of Montreal begins to the west of Maskinongé, Quebec and Yamaska and ends at the extremity of the inhabited area, namely fort Saint-Jean, Châteauguay and Vaudreuil.

1713 – Michel Bégon decides to erect stone fortifications. The wooden walls are replaced with stone due to the threat of British attack.

1717–1744 – Stone fortifications were erected according to plans by the architect Gaspard-Joseph Chaussegros de Léry. The fortifications correspond roughly to the present-day limits of Old Montreal, with Rue Berri to the east, Rue de la Commune to the south, Rue McGill to the west, and Ruelle de la Fortification to the north.

1719 – Pointe-aux-Trembles windmill is built at the corner of Notre-Dame Street and Third Avenue. Its three storeys make it the tallest windmill in Quebec that still stands.

1721 – The great fire. New wood constructions are prohibited inside city limits.

1726 – A dam is built to link the river bank to the Île de la Visitation – one of the most impressive feats of civil engineering of the French regime. It remains in operation until 1960.

1731 – Orchards covered 90 arpents (76 acres; 31 ha) on the Île de Montréal, on the side of the mountain and around town. From 1731 to 1781, the surface area occupied by the orchards rise from 90 to 402 arpents (76 to 340 acres; 31 to 137 ha).

1737 – Inauguration of the Chemin du Roy on the North Shore (Laval) between Montréal and Quebec City. The road's construction takes 4 years and requires the construction of 13 bridges. After its completion, people can travel from one city to the other in 4 days.

1749-51 – De la Visitation Church (1747 Gouin Boulevard) is built to replace the small chapel at Fort Lorette. It is the oldest church in Montreal and the only one built during the old régime still standing. The church is consecrated by Henri-Marie Dubreil de Pontbriand in 1752.

1760 – The British, under General Jeffrey Amherst, march from Lachine through Nazareth Fief (the name used for Griffintown at this time), through the Recollet Gate and into the walled city of Montreal. The Articles of Capitulation of Montreal are signed on September 8, in the British camp before the city of Montréal. Most of the North American fighting ends with the surrender of Montréal.

1775 – Montreal falls without any significant fighting on November 13, as Carleton, deciding that the city was indefensible (and having suffered significant militia desertion upon the news of the fall of St. Johns), withdraws.

1775 – Richard Montgomery uses some of the captured boats to move towards Quebec City with about 300 troops on November 28, leaving about 200 in Montreal under the command of General David Wooster.[16]

1776 – May – With only 1,765 soldiers remaining in Montreal, the colonial force is overcome by the British.

1776 – Within four hours, Benedict Arnold and the American forces garrisoned around Montreal abandon the city (but not before trying to burn it down), leaving it in the hands of the local militia. Carleton's fleet arrive in Montreal on June 17.[17]

1789 – Lord Grenville proposes that land in Upper Canada be held in free and common soccage, and that the tenure of Lower Canadian lands be optional with the inhabitants.

1789 – May 4 – The justices of the peace, who govern Montreal's affairs, order "the price and assize of bread, for this month" to be: "the white loaf of 4lbs. at 13d., or 30 sous", etc., and that bakers of the city and suburbs do conform thereto, and mark their bread with their initials.

1789 – Christ Church opens for service on December 20.

1791 – Edmund Burke supports the proposed constitution for Canada, saying that "To attempt to amalgamate two populations, composed of races of men diverse in language, laws and habitudes, is complete absurdity. Let the proposed constitution be founded on man's nature, the only solid basis for an enduring government."

1792 – December 20 – a fortnightly mail is established between Canada and the United States.

1803-15 – With the Napoleonic Wars comes a demand for large amounts of squared timber for shipbuilding. Montreal is able to fulfil the demand, and this expansion of the city's economic base is reflected in a rise in population to 26,154 by the year 1825.

1804-17 – The demolition of Montreal's fortifications takes 13 years, from 1804 to 1817.

1805 – Thomas McCord returns to Montreal and recovers his land, which has been divided by Mary Griffin into streets and lots. The name Griffintown sticks.

1809 – November 3 – John Molson's steamboat PS Accommodation sails from Montreal to Quebec. It is 85 feet over all, has a 6 horse-power engine, makes the distance in 36 hours, but stops at night and reaches Quebec on the 6th. The PS Accommodation is the second steamboat in America and probably in the world. The fare for an adult is £2.10s.od =$10.

1816 – May 14 – Thomas A. Turner and Robert Armour, Esq., are appointed commissioners for the improvement of internal navigation between Montreal and Lachine, under the Provincial Act 48 George III,c. 19.

1821 – The British garrison starts the construction of the Fort de l'Île Sainte-Hélène. It is completed in 1823 and partially rebuilt in 1863 after a fire as a preventive measure against an eventual American attack.

1825 – The Lachine Canal is opened, and new industries spring up in the St. Antoine ward area as a direct outcome of the easier transport of goods. Shipping immediately increases and, along with the destruction of the city walls, Montreal comes to be an economic, rather than military, city. Gradually, the city's harbour facilities expand. In 1830 the wharves are rudimentary and stretched for only a short distance along De la Commune Street.

1825 – First permanent theatre building in Montreal, Theatre Royal, is built by John Molson to attract bigger names to the city, which lacked such a venue. It costs the magnate $30,000. The building is demolished in 1844 and the site was used for the Bonsecours Market. Another venue, also called Theatre Royal, was built not far away in Old Montreal; this building, too, no longer exists.

1841 – There are now at least 6,500 Irish Catholics in Montreal. Most of the immigrants to Montreal settle in Griffintown, particularly in the area west of McGill Street (Montreal). In this district, the area between the Lachine Railroad and the Lachine Canal becomes a slum. Much like the French slums of Hochelaga Maisonneuve to the east.

1854 – St. Ann's Church is consecrated, becoming the centre of Griffintown life; it opens on December 8 (Feast of the Immaculate Conception) and was designed by John Ostell. The Sulpicians donated the land for the church and provided the Irish-born pastors: Father Michael O'Brien, Father Michael O'Farrell and Father James Hogan (priest 1867–1884). Some residents of Griffintown claim that St. Ann's ("down the hill") was actually more of a center for the Irish in Montreal than St. Patrick's Basilica, Montreal's ("up the hill") was, since most of the city's Irish lived in Griffintown.

1864 – The Montreal City Passenger Railway Company has 10 miles of track, $240,000 paid capital and carries 1,485,725 passengers at 5 cents each.

1864 – In October, delegates from across British North America developed the terms for Confederation at a three-week conference in Quebec City. After the Quebec Conference, there remained the task of selling Confederation to the citizens.

1865 – July 11–14 – Convention at Detroit to promote a new Reciprocity treaty. Montrealers attend, but only to give desired information. The Convention passes resolutions favouring a new Reciprocity treaty.

1879 – Mary Gallagher is murdered by jealous rival Susan Kennedy on June 27. It is a sensational story. It's said Gallagher's ghost returns every seven years to haunt Griffintown.

1879 – In a strange turn of events, Michael Flanagan, cleared of all charges regarding the death of Mary Gallagher, is loading barges in the Wellington Basin when he falls and drowns on December 5, the very same day Susan Kennedy was supposed to be hanged.

1892 – The era of public transportation in Montreal begins with the inauguration of the electric tram. The trams constitute a practical way to get from one end of the city to the other, especially for workers.

1897 – A survey of living conditions is conducted by Mr. Herbert Brown Ames. He points out the discrepancy in living conditions between wealthy areas of Montreal ('the upper city') and the areas inhabited by the working class ('the city below the hill'): "The sanitary accommodation of 'the city below the hill' is a disgrace to any nineteenth century city on this or any other continent. I presume there is hardly a house in all the upper city without modern plumbing, and yet in the lower city not less than half the homes have indoor water-closet privileges. In Griffintown only one home in four is suitably equipped, beyond the canal (in Pointe-Saint-Charles) it is but little better. Our city by-law prohibits the erection of further out-door closets, but it contains no provision for eradicating those already in use."

1899 – October 30 – The First Canadian Contingent of the Boer War sets sail to South Africa on the SS Sardinian of the Allan Line, bearing Canada's initial quota of fighting men, including the men of "E Company" of Montreal.

1899 – In the afternoon of November 21, Montrealers see their first car. At the wheel of this first steam-powered automobile is Ucal-Henri Dandurand, accompanied by Mayor Raymond Préfontaine. They descend steep Côte du Beaver Hall without difficulty and climb back up through the streets in the same fashion.

1901 – The city counted 1033 men and 4 women in the Chinese community. Clustered together along Saint Laurent Boulevard and De la Gauchetière Street, various Chinese establishments also serve as living quarters for the first Chinese Montrealers and, from the end of the 19th century onwards, constitute a distinctive neighbourhood: Chinatown.

2012 - Gérald Tremblay steps down as mayor in November after allegations of serious irregularities in party financing. Michael Applebaum becomes interim mayor until municipal elections in November 2013

2013 - Michael Applebaum is arrested and indicted with 14 charges including fraud and corruption. He steps down. City councillors elect Laurent Blanchard to serve as mayor for the four months remaining before the municipal elections.